Head of Revenue, Overtime
Why Join Us
Receivables management is a $20B+ market at an inflection point. Increasing regulatory complexity, rising operating costs, and declining effectiveness of legacy outbound models are driving demand for a modern, AI-first approach. Overtime.ai is the platform to define this next generation—combining voice AI, automation, and compliance-by-design to transform how the industry recovers debt while improving the consumer experience. This is a start-up leadership opportunity to shape go-to-market strategy, build a category-defining sales motion, and drive revenue in a market ready for disruption.
The Head of Revenue Development & Strategic Growth is responsible for building pipeline through partnerships, market engagement, and early customer programs for the Overtime.ai platform.
This role works in close partnership with the Head of Sales to support deal development and accelerate revenue. All qualified opportunities and revenue generated through this role are credited to the Sales organization and count toward the Head of Sales’ pipeline and quota. The role reports to the CEO and is tightly aligned with Sales on priorities, pipeline development, and field execution.
Requirements
10+ years in enterprise software, fintech, or receivables management
Experience building partnerships or new revenue channels
Strong communication and industry presence
Comfortable working across teams without direct authority
Responsibilities
Revenue Development
Build pipeline through partnerships, industry relationships, and targeted outreach
Develop early-stage opportunities and transition them into the sales pipeline
Support new channels that strengthen overall sales performance
Partnerships
Develop and manage strategic partners (platforms, integrations, industry relationships)
Create opportunities that drive distribution and embedded adoption
Act as a senior point of contact for key partners
Sales Collaboration
Work closely with the Head of Sales on key opportunities
Support early deal shaping, use cases, and positioning
Participate in select sales cycles as needed
Ensure smooth handoff of opportunities to Sales for execution and close
Beta and Early Customers
Build and manage beta and pilot programs
Identify the right early customers and use cases
Drive conversion from pilot to paying customer in coordination with Sales
Market Engagement
Build relationships across agencies, healthcare, and financial services
Represent Overtime.ai in the market and at industry events
Identify new use cases and opportunities
Alignment
Partner with Sales on target markets and priorities
Align with Marketing, Product, and Operations
Provide market feedback to improve positioning and execution
What we offer
A team built from the collections industry — work alongside leaders with experience across third party collections, healthcare revenue cycle, and first party servicing.
Opportunity to grow with the company — take on meaningful responsibility as the business expands.
Fast moving environment with direct access to leadership — decisions get made quickly and ideas can move into execution without unnecessary layers.
Build technology tied to real operational outcomes — focused on improving recovery performance, lowering operating costs, and creating a better consumer experience in regulated environments.
Fully remote within the US
15 days PTO + all federal holidays + 3 sick days
Health insurance reimbursement (ICHRA)
401(k)
Laptop provided by the company
Participation in Employee Stock Ownership Plan (ESOP)
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